Isobutyl chloroformate → 4-Chloro-4'-methylmercaptomethylbenzophenone isobutoxycarbonyl hydrazone

HRID 1421543Notes

Reaction equation

HRID 1421543 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6](=[N:16][NH2:17])[C:7]2[CH:12]=[CH:11][C:10]([CH2:13][S:14][CH3:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:20](Cl)(=[O:26])[O:21][CH2:22][CH:23]([CH3:25])[CH3:24]>CN(C1C=CN=CC=1)C.ClCCl>[CH2:22]([O:21][C:20]([NH:17][N:16]=[C:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][S:14][CH3:15])=[CH:9][CH:8]=1)[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][CH:18]=1)=[O:26])[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 62365Isobutyl chloroformateHCID 857041584-Chloro-4'-methylmercaptomethylbenzophenone hydrazone

Product 1

HCID 539980974-Chloro-4'-methylmercaptomethylbenzophenone isobutoxycarbonyl hydrazoneYield 24.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (30 ml) of 4-chloro-4'-methylmercaptomethylbenzophenone hydrazone (1.5 g) and 4-(N,N-dimethylamino)pyridine (1.2 g), isobutyl chlorocarbonate (0.8 g) was dropwise added under cooling with ice and subsequently stirred at a room temperature for 20 hours. The reaction mixture was then successively washed with 2N hydrochloric acid, water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:4) to obtain 4-chloro-4'-methylmercaptomethylbenzophenone isobutoxycarbonyl hydrazone (0.5 g) as an isomer mixture.

Workup

  1. temperatureunder cooling with ice
  2. washThe reaction mixture was then successively washed with 2N hydrochloric acid, water
  3. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-634b589ad6f847c997c2e38fd862ead8
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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